Linear silmethylenesiloxane



Patented Nov. 2, 1948 UNITED s'rres 2.452.895 LINEAR smmnrnynsnnsmoxnnaBeen A. Bluestein, Schenectady, N. Y., assignor to General ElectricCompany, a corporation ed New York No Drawing. Application .lanuary 22,1948,

Serial No. 3.812

1 he. in L where n and m are each Whole numbers equal to one of thefollowing: 1,2.

The compounds of this invention have utility as intermediates in thepreparation of other chemical compounds and polymers. These compoundsmay also be employed for lubricating purposes and as anti-foamingagents. In addition, under suitable conditions of reaction, the claimedcompositions of matter may be converted to higher molecular weightliquid or elastic polymeric materials which may be employed in thepreparation of novel synthetic resins and rubbers.

The following examples are illustrative of procedures whereby my claimedcompositions of matter may be prepared. It will, of course, be apparentto those skilled in the art that other methods may be employed inpreparing these novall compounds.

EXAMPLE 1 A solution of 540 cc. (2.5 mole)monochloromethyipentamethyldisiloxane E(CH3)3S1OSi(CH:)zCH2Cll in 500cc. anhydrous ethyl ether was added slowly to 65 grams (2.8 mols)magnesium and 50 cc. dry

ethyl ether. The desired reaction between the ingredients was initiatedby a crystal of iodine. The addition took place over a two-hour period.

4% Claims. (C1. 260-4482) The mixture was heated at reflux temperaturefor 15 minutes after the addition was complete.

Thereafter, 145 cc. (1.2 mols) dimethyldichlorosilane was added during aV2 hour period and the mass was heated at its reflux temperature forabout 2 hours. The contents of the reaction vessel were poured ontoabout 2 kg. cracked ice and water. the ether layer separated and Washedthree times with water and dried over anhydrous NazSOi. The resultingcolorless liquid was distilled through a Vigreaux column to remove theether and other materials boiling below 105 C. The residue was thenrapidly distilled at mm. to a temperature of 235 C. and the distillatecarefully fractionally distilled to yield the following chemicalcompounds having the stipulated physical properties:

Table i Molar Reflectivity Compound B. P. O. all" no Found Cale.

:1?,2,4,4,(3,o-hexemethyld-oxe-ZAfl-trisilaheptane having the form a 0Hi 0 Ha C Ht 0 Ha Si-C Hri--G--Si-CH;

C Ha Ha 0 Ha 13is-(pentaniethyldisiloxanyl) methane or 2,2,4,4,6,6,8B-octamethyl-3,741ioxa-2,4,6,8-tetrasilanonane corresponding to theformula C Ht C Ht l. l.. H. Ha (5H2: s

a Dimothyl-bis-(pentemethyldisiloxanylmethyl) silane or 2,2,4,t,6,6,83,10,10decamethyl-3,9-dioxa-2,4,o,8,lO-peutasilaundecenecorresponding to the formula CH: CH3 CH2 HaB l0-S lO Bit- 1 Ha 5H1; .v gJIHB Analysis of the aforementioned compounds showed them to contain theiollowing per cents of carbon and hydrogen:

Totals 2 er Cent Per Cent Hydrogen Carbon Compound Found Cale. FoundGale WHPLE 2 ing between about 118 C. to about 130 C. at approximately52-54 mm. This fraction, which was believed to comprise an azeotropicmixture of his- (pentamethyldisiloxanyl)methane and 2.2.4.45-pentamethyl-3-oxa-6-hydroxy 2,4,6 trisilaheptane having the formula 7CH: OH HI) lSi-O-dF-C Hr-AIC HI was heated at reflux temperature forabout 3 hours and thereafter fractionaliy distilled to yield tetramethyl1,3 bis (pentamethyldisiloxanylmethyl) disiloxane or2,2,4,4,6,6,8,8,10,10,12,12-dodecamethyl 3,7,11trioxa-2,4,6,8,10,12-hexasilatridecane corresponding to the formula HaCH3 Hz Analysis 01 this compound showed it to contain contain 42.70 percent carbon (calc. 42.25% and 10.30 percent hydrogen (calc. 10.20%).This compound has the following properties:

may be prepared by treatingdimethyl-bis-(pentamethyldisiloxanylmethyl)silane with concentratedsulphuric acid; diluting the mixture with water, separating and washingthe organic layer with water, and drying and fractionally distilling thedried organic residue.

What I claim as new and desire to secure by Letters Patent of the UnitedStates is:

1. Chemical compounds corresponding to the general formula 011 on I lwhere m and n are each a whole number equal to from 1 to 2.

2. 2,2,4,4,6,6,8,8, octamethyl- 3,7-dioxa-2,4,6,8- tetrasilanonanecorresponding to the formula 3.2,2,4,4,6,6,8,8,10,10-decamethyl-3,9-dioxa2,- 4,6,8,10-pentasilaundecanecorresponding to the CH3 CH3 2 CH3 4. 2,2,4,4,6,6,8,8,10,10,12,12dodecamethy1-3,'l- 11 trioxa 2,4,6,8,10,12-hexasilatridecanecorresponding to the formula C H 0 H3 0 Ha BEN A. BLUESTEIN.

REFERENCES CITED The following references are of record in the file ofthis patent;

UNITED STATES PATENTS Name Date Spier July 6, 1948 OTHER REFERENCESGoodwin, JACS, vol. 69 (1947), page 2247. Sommer, JACS, vol. 69 (1937),page 980.

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